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Record Information
Version1.0
Creation Date2016-05-19 01:31:15 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003980
Identification
Common NameAmitrole
ClassSmall Molecule
DescriptionA member of the class of triazoles that is 1H-1,2,4-triazole substituted by an amino group at position 3. Used to control annual grasses and aquatic weeds (but not on food crops because it causes cancer in laboratory animals). Its use within the EU was banned from September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
1H-1,2,4-Triazol-3-ylamineChEBI
2-Amino-1,3,4-triazoleChEBI
3-Amino-1,2,4-triazoleChEBI
3-Amino-S-triazoleChEBI
3-ATChEBI
AminotriazoleChEBI
AmitroleMeSH
Chemical FormulaC2H4N4
Average Molecular Mass84.080 g/mol
Monoisotopic Mass84.044 g/mol
CAS Registry Number61-82-5
IUPAC Name2,3-dihydro-1H-1,2,4-triazol-3-imine
Traditional Name3-amino-1,2,4-triazole
SMILESN=C1NNC=N1
InChI IdentifierInChI=1S/C2H4N4/c3-2-4-1-5-6-2/h1H,(H3,3,4,5,6)
InChI KeyKLSJWNVTNUYHDU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triazoles. Triazoles are compounds containing a five-member aromatic ring of two carbon atoms and three nitrogen atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassTriazoles
Direct ParentTriazoles
Alternative Parents
Substituents
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.5 g/LALOGPS
logP-2.1ALOGPS
logP-1.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)6.15ChemAxon
pKa (Strongest Basic)15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.27 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity52.38 m³·mol⁻¹ChemAxon
Polarizability7.34 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03di-6890000000-754b3b51d99b00d9a12aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-000i-3940000000-d9c82cecc0ca53dbd9b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-c99f58af7e45f848dbdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-f365faf2b853da634152View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-af199e373854b1891b2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-99a9f3545fabfc75dbadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-f5d4b0203fe8de3b4a09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-817d8db3192407931ec9View in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD0-1491
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAmitrole
Chemspider IDNot Available
ChEBI ID40036
PubChem Compound ID1639
Kegg Compound IDC11261
YMDB IDNot Available
ECMDB IDECMDB20503
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11673067
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17549540
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25820916
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=7546330
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=7986209